Mr Black did not turn out to be much of an industrialist - the farm-machinery company, the grocery chain, the brewer and mines were disposed of. Rather, it was his interest in amateur history and a chance entry into newspapers that turned him into a media magnate.
Today, as chief executive of Hollinger, he controls a global network of 250 newspapers, including those in Canada's Southam chain, which reach more than 50 per cent of the country's total readership.
Mr Black sees himself as a heroic figure, with an enduring interest in Napoleon, and prides himself on his knowledge of 19th and 20th-century wars. He used to spend time with his friend, Hal Jackson, the former lieutenant-governor of Ontario, re-creating famous battles with model soldiers.
Mr Black's academic career was marred when he was expelled from Upper Canada College, an elite private school, for breaking into the headmaster's office, stealing copies of the final exam and selling them to his classmates. He eventually graduated from university in law.
Later he purchased a failing English-language daily in Eastern Quebec for a pittance. He exhibited the same opportunism to gain control of the Daily and Sunday Telegraph when the Berry family got into financial difficulties.
Mr Black has spent a lifetime making contacts ranging from the former US secretary of state Henry Kissinger to Baroness Thatcher.
He also prides himself on his vocabulary, and is quick to dismiss those whose intellect he considers inferior. When the Canadian author John Ralston Saul criticised his business acumen, Mr Black dismissed him as someone who has "sniggering, puerile, defamatory and cruelly limited talents."